24
2 Results and Discussion
Table 3: Conditions for a one-pot amination – rearrangement reaction. NMR yields were
determined with 1,3,5-trimethoxybenzene as an internal standard. (Adapted
from Gonçalves et al. 2019, https://pubs.acs.org/doi/10.1021/jacs.
9b06956; with kind permission from © ACS Publications 2020. All Rights Reserved)
entry solvent
Step 1
Step 2
NMR
yield
2.1b
NMR
yield
2.3a
1
MeCN
NaH + sulfonamide
supended in MeCN
(0.12 M)
3 eq. Pr4NOH
32
0
2
MeCN
Na-sulfonamidate
10 eq. Pr4NOH
4
19
3
MeCN
Na-sulfonamidate
+ 2 eq. TBAHFP
10 eq. Pr4NOH
1
15
4
DCM
NaH + sulfonamide
in DMF (0.6 M)
Addition of 3
mL MeCN, 10
eq. Bu4NOH
70
0
5
DCM
NaH + sulfonamide
in DMF (0.6 M)
Addition of 3
mL dioxane, 10
eq. Bu4NOH
69
0